1H-1,2,4-Triazole → HCID 54529319, compound

HRID 1980522Notes

Reaction equation

HRID 1980522 reaction equation
[H-].[Na+].[NH:3]1[CH:7]=[N:6][CH:5]=[N:4]1.[F:8][C:9]1[CH:14]=[CH:13][C:12]([Si:15]([C:20]2[CH:25]=[CH:24][C:23]([F:26])=[CH:22][CH:21]=2)([CH:17](Cl)[CH3:18])[CH3:16])=[CH:11][CH:10]=1.FC1C=CC([Si](C2C=CC(F)=CC=2)(CCCl)C)=CC=1>CN(C)C=O.O.ClCCl.CO>[F:26][C:23]1[CH:24]=[CH:25][C:20]([Si:15]([C:12]2[CH:11]=[CH:10][C:9]([F:8])=[CH:14][CH:13]=2)([CH3:16])[CH:17]([N:3]2[CH:7]=[N:6][CH:5]=[N:4]2)[CH3:18])=[CH:21][CH:22]=1

Participants

9

Reactant 4

HCID 92571H-1,2,4-TriazoleHCID 24758Sodium hydrideHCID 20401745HCID 20401745, compoundHCID 20401762HCID 20401762, compound

Product 1

HCID 54529319HCID 54529319, compoundYield 12%

Reagents, catalysts & solvents 4

HCID 887MethanolSolventHCID 962WaterSolventHCID 6228DimethylformamideSolvent2×HCID 6344DichloromethaneSolvent2×

Procedure

A mixture of 1.78 g (37 mmol) of 50% sodium hydride, 30 ml of dimethylformamide, and 2.56 g (37 mmol) of 1H-1,2,4-triazole was stirred at 50° for one hour, and a solution of 10 g (33.7 mmol) of a 1:1 mixture of bis(4-fluorophenyl)-1-chloroethyl(methyl)silane and bis(4-fluorophenyl)-2-chloroethyl(methyl)silane in 10 ml of dimethylformamide was added. The mixture was stirred at 50° for 64 hours, cooled, diluted with water, and extracted with ether. The ether extracts were washed with water and brine, dried over sodium sulfate, and evaporated to leave a viscous oil. Chromatography over silica gel eluting with dichloromethane followed by 3% methanol in dichloromethane provided 1.37 g (12%) of the title compound as a viscous oil: nmr (CDCl3) 0.7 (3H, s), 1.6 (3H, d, J=7 Hz), 4.5 (1H, q, J=7 Hz), 6.9-7.7 (8H, m), 7.9 (1H, s), and 8.0 (1H, s).

Workup

  1. additionwas added
  2. stirringThe mixture was stirred at 50° for 64 hours
  3. temperaturecooled
  4. extractionextracted with ether
  5. washThe ether extracts were washed with water and brine
  6. dry with materialdried over sodium sulfate
  7. customevaporated
  8. customto leave a viscous oil

Sources & evidence

ORD record
ord-8503518506be4bdaaaa37734ef390892
Source dataset
uspto-grants-1985_04
Patent number
US04510136

Reaction notes

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